CN112778916A - Special fluorine-containing pressure-sensitive adhesive and preparation method thereof - Google Patents
Special fluorine-containing pressure-sensitive adhesive and preparation method thereof Download PDFInfo
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- CN112778916A CN112778916A CN202011616208.8A CN202011616208A CN112778916A CN 112778916 A CN112778916 A CN 112778916A CN 202011616208 A CN202011616208 A CN 202011616208A CN 112778916 A CN112778916 A CN 112778916A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
- C09J7/22—Plastics; Metallised plastics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09J133/16—Homopolymers or copolymers of esters containing halogen atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/20—Presence of organic materials
- C09J2400/22—Presence of unspecified polymer
- C09J2400/226—Presence of unspecified polymer in the substrate
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2433/00—Presence of (meth)acrylic polymer
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a special fluorine-containing pressure-sensitive adhesive which is characterized by comprising an adhesive and a base material, wherein the adhesive is coated on one side surface of the base material; the adhesive comprises a component A and a component B; the component A comprises the following components in percentage by mol: 5-50% of a pentafluorobenzene-containing functional monomer; the initiator is 0.1% -0.5%; the soft monomer accounts for 50% -95%; the hard monomer is 0% -50%; 0% -50% of a cross-linking agent; the component B is a solvent, and the mole number of the component B is 3-8 times of the total mole number of the component A. The special pressure-sensitive adhesive of the invention has better guarantee on cohesive force, solvent resistance, adhesive force and the like during bonding aiming at the fluorine-containing polymer material, has high crosslinking speed and simultaneously has no solvent discharge. The invention also provides a preparation method of the special fluorine-containing pressure-sensitive adhesive, and provides a new thought and development direction for the development of the pressure-sensitive adhesive.
Description
Technical Field
The invention relates to the technical field of fluorine-containing materials, in particular to a special fluorine-containing pressure-sensitive adhesive and a preparation method thereof.
Background
With the rapid increase of national economy, a large number of fluorine-containing products are coming into various fields of aviation, environmental protection, communication, medical treatment and the like. The pressure-sensitive adhesive is used as a part of the adhesive, can be instantly adhered at room temperature because the pressure-sensitive adhesive is a pressure-sensitive adhesive material, and has the excellent properties of being capable of being adhered to the surfaces of various base materials only by slight pressure load, having no residue after the base materials are peeled off, and the like.
When the base material is made of inert material, the adhesive has poor adhesion effect on the inert material due to high non-polarity, low surface energy and poor wettability of the inert material. For the adhesion of inert materials, the surface of the material is subjected to sexual pretreatment, functional groups such as hydroxyl groups are introduced, the reaction degree of the adhesive and the surface of the material is improved, and the bonding strength of the adhesive and the surface of the material is further enhanced. However, the pretreatment method requires special equipment, is expensive, and causes damage to the surface of the material after the treatment.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a special fluorine-containing pressure-sensitive adhesive and a preparation method thereof, so as to solve the problems that the prior art has poor bonding effect between an adhesive and the surface of a material, needs special equipment for treatment, has high cost and can damage the surface of the material.
In order to solve the technical problems, the invention adopts the following technical scheme:
the special fluorine-containing pressure-sensitive adhesive comprises an adhesive and a base material, wherein the adhesive is coated on one side surface of the base material; the adhesive comprises a component A and a component B;
the component A comprises the following components in percentage by mol: 5 to 50 percent of pentafluorobenzene-containing functional monomer; 0.1 to 0.5 percent of initiator; the soft monomer accounts for 50 to 95 percent; 0 to 50 percent of hard monomer; 0 to 50 percent of cross-linking agent.
The component B is a solvent, and the mole number of the component B is 3-8 times of the total mole number of the component A.
Preferably, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, and the soft monomer comprises butyl acrylate, ethyl acrylate and isooctyl acrylate.
Preferably, the hard monomer comprises methyl methacrylate and styrene.
Preferably, the crosslinking agent is a glycidyl methacrylate crosslinking agent.
Preferably, the initiator is azobisisobutyronitrile.
Preferably, the solvent is ethyl acetate.
The invention provides a preparation method of a monomer with a pentafluorobenzene function, which comprises the following steps:
adding a fluorine-containing benzene structure compound and acrylic acid or acryloyl chloride into a reactor, heating for reaction, and extracting, cleaning and separating to obtain the monomer containing the pentafluorobenzene function.
Preferably, the molar mass ratio of the fluorobenzene structure-containing compound to acrylic acid or acryloyl chloride is (1-3): (1-4) the reaction time is 2-3 h.
The invention also provides a preparation method of the special fluorine-containing pressure-sensitive adhesive, which comprises the following steps:
(1) under the protection of argon, adding a solvent and other raw materials into a reactor according to the formula of the invention, finally adding an initiator for heating reaction, and washing and drying to obtain a pure polymer;
(2) and (2) coating the polymer obtained in the step (1) on a fluorine-containing polymer material to obtain the special fluorine-containing pressure-sensitive adhesive.
Preferably, the fluoropolymer material in step (2) is a fluoropolymer membrane.
Compared with the prior art, the invention has the following beneficial effects:
1. the special fluorine-containing pressure-sensitive adhesive is prepared by using a pentafluorobenzene-containing functional monomer as a raw material and matching a soft monomer, a hard monomer, a crosslinking agent and a solvent; aiming at materials with low surface tension, particularly fluorine-containing materials, the special fluorine-containing pressure-sensitive adhesive has excellent adhesive property, introduces fluorine element to acrylic ester, reduces the surface energy of the pressure-sensitive adhesive, and improves the adhesive strength of the pressure-sensitive adhesive to inert materials, particularly fluorine-containing materials; meanwhile, due to the fact that the fluorocarbon bond energy is large and groups contained in a benzene ring are introduced, irregular winding of the fluorocarbon chain is reduced, and the bonding performance of the special fluorine-containing pressure-sensitive adhesive is remarkably improved.
2. The invention mainly aims at materials with lower surface tension, particularly fluorine-containing materials, the preparation method adopted by the invention does not need special equipment to pretreat the surface of a base material, the preparation process is simple, the production cost is lower, the special fluorine-containing pressure-sensitive adhesive can be obtained only by directly coating the prepared adhesive on the surface of the fluorine-containing polymer material, the integrity of the surface of the fluorine-containing polymer material is well ensured, meanwhile, the adhesive and the fluorine-containing polymer material have excellent bonding strength, and the pressure-sensitive adhesive prepared by the invention has excellent initial adhesion, holding adhesion and peeling resistance.
3. The invention provides a new thought and development direction for the development of the pressure-sensitive adhesive, and the pressure-sensitive adhesive has better guarantee on the cohesive force, solvent resistance, adhesive force and the like of the fluorine-containing polymer material during bonding, has high crosslinking speed and does not discharge solvent.
Detailed Description
The present invention will be further described with reference to the following examples.
Special fluorine-containing pressure-sensitive adhesive
The special fluorine-containing pressure-sensitive adhesive comprises an adhesive and a base material, wherein the adhesive is coated on one side surface of the base material; the adhesive comprises a component A and a component B;
the component A comprises the following components in percentage by mol: 5 to 50 percent of pentafluorobenzene-containing functional monomer; 0.1 to 0.5 percent of initiator; 50-95% of soft monomer, 0-50% of hard monomer and 0-50% of cross-linking agent;
the component B is a solvent, and the mole number of the component B is 3-8 times of the total mole number of the component A.
In specific implementation, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the pentafluorobenzene-containing functional monomer is prepared from a fluorobenzene-containing structural compound, and the soft monomer comprises butyl acrylate, ethyl acrylate and isooctyl acrylate. The hard monomer comprises methyl methacrylate and styrene. The cross-linking agent is glycidyl methacrylate cross-linking agent. The initiator is azobisisobutyronitrile. The solvent is ethyl acetate.
The special fluorine-containing pressure-sensitive adhesive provided by the invention mainly aims at materials with lower surface tension, particularly comprises fluorine-containing materials, and has excellent adhesive property.
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive described in embodiments 1 to 5, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is butyl acrylate, the hard monomer is methyl methacrylate, and the crosslinking agent is methyl methacrylate, and the specific amounts are shown in table 1.
TABLE 1
Raw materials (mol) | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 |
Acrylic acid butyl ester | 8 | 7 | 6 | 5 | 4 |
Acrylic acid pentafluorobenzyl ester | 1 | 1 | 1 | 1 | 1 |
Methacrylic acid methyl ester | 1 | 2 | 3 | 4 | 5 |
Azobisisobutyronitrile | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
Ethyl acetate | 40 | 40 | 40 | 40 | 40 |
The initial adhesion of the examples is tested by using a GB-4852-1984 pressure sensitive adhesive tape initial adhesion test method (rolling ball method), the permanent adhesion of the examples is tested by using a GB/T-4851-1998 adhesive tape permanent adhesion test method, the peel strength of the examples is tested by using a GB/T-4851-1998 adhesive tape peel strength test method, and the relevant performances of the examples 1-5 are shown in Table 2.
TABLE 2
Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
Initial viscosity (ball) | 17 | 22 | 16 | 14 | 10 |
Viscosity (time/min) | 45 | 54 | 63 | 46 | 55 |
180 DEG peeling off [ N/25mm ]] | 12.3 | 9.3 | 14.1 | 10.7 | 11.6 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive in embodiments 6 to 10, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is butyl acrylate, the hard monomer is styrene, and the crosslinking agent is glycidyl methacrylate, and the specific amount is shown in table 3.
TABLE 3
Raw materials (mol) | Example 6 | Example 7 | Example 8 | Example 9 | Example 10 |
Acrylic acid butyl ester | 3 | 2.5 | 2 | 1.5 | 1 |
Acrylic acid pentafluorobenzyl ester | 1 | 1 | 1 | 1 | 1 |
Styrene (meth) acrylic acid ester | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
Glycidyl methacrylate | 0.5 | 1 | 1.5 | 2 | 2.5 |
Azobisisobutyronitrile | 0.025 | 0.025 | 0.025 | 0.025 | 0.025 |
Ethyl acetate | 20 | 20 | 20 | 20 | 20 |
The same detection method as that used in examples 1 to 5 was used to perform the performance detection of examples 6 to 10, and the detection results are shown in Table 4.
TABLE 4
Example 6 | Example 7 | Example 8 | Example 9 | Example 10 | |
Initial viscosity (ball) | 23 | 22 | 17 | 10 | 5 |
Viscosity (time/min) | 88 | 120 | 340 | 380 | 600 |
180 DEG peeling off [ N/25mm ]] | 9.4 | 10.2 | 13.4 | 13.6 | 15.7 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive in embodiments 11 to 15, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is butyl acrylate, and no hard monomer and no crosslinking agent are added, and the specific amount is shown in table 5.
TABLE 5
Raw materials (mol) | Example 11 | Example 12 | Example 13 | Example 14 | Example 15 |
Acrylic acid butyl ester | 9 | 4 | 2.5 | 1.5 | 1 |
Acrylic acid pentafluorobenzyl ester | 1 | 1 | 1 | 1 | 1 |
Azobisisobutyronitrile | 0.05 | 0.025 | 0.0165 | 0.0125 | 0.01 |
Ethyl acetate | 40 | 20 | 13.2 | 10 | 8 |
The same test methods as those used in examples 1 to 5 were used to test the performances of examples 11 to 15, and the correlation performances are shown in Table 6.
TABLE 6
Example 11 | Example 12 | Example 13 | Example 14 | Example 15 | |
Initial viscosity (ball) | 21 | 20 | 24 | 22 | 18 |
Viscosity (time/min) | 45 | 78 | 63 | 72 | 88 |
180 DEG peeling off [ N/25mm ]] | 12.3 | 15.6 | 11.4 | 10.7 | 12 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive described in embodiments 16 to 19, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is butyl acrylate, no hard monomer is added, and the crosslinking agent is methyl methacrylate, and the specific amount is shown in table 7.
TABLE 7
Raw materials (mol) | Example 16 | Example 17 | Example 18 | Example 19 |
Acrylic acid butyl ester | 3.5 | 3 | 2.5 | 2 |
Acrylic acid pentafluorobenzyl ester | 1 | 1 | 1 | 1 |
Glycidyl methacrylate | 0.5 | 1 | 1.5 | 2 |
Azobisisobutyronitrile | 0.025 | 0.025 | 0.025 | 0.025 |
Ethyl acetate | 20 | 20 | 20 | 20 |
The same detection methods as those used in examples 1 to 5 were used to further detect the properties of examples 16 to 19, and the correlation properties are shown in Table 8.
TABLE 8
Example 16 | Example 17 | Example 18 | Example 19 | |
Initial viscosity (ball) | 18 | 15 | 6 | 3 |
Viscosity (time/min) | 62 | 73 | 88 | 140 |
180 DEG peeling off [ N/25mm ]] | 11.9 | 14.5 | 13.2 | 15 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive of embodiments 20 to 24, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is ethyl acrylate, the hard monomer is methyl methacrylate, and no crosslinking agent is added, and the specific amount is shown in table 7.
TABLE 9
Raw materials (mol) | Example 20 | Example 21 | Example 22 | Example 23 | Example 24 |
Acrylic acid ethyl ester | 8.5 | 7.5 | 6.5 | 5.5 | 4.5 |
Acrylic acid pentafluorobenzyl ester | 1 | 2 | 3 | 4 | 5 |
Methacrylic acid methyl ester | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
Azobisisobutyronitrile | 0.025 | 0.025 | 0.025 | 0.025 | 0.025 |
Ethyl acetate | 30 | 30 | 30 | 30 | 30 |
The same detection method as that used in examples 1 to 5 was used to detect the performance of examples 20 to 24, and the correlation properties are shown in Table 10.
Watch 10
Example 20 | Example 21 | Example 22 | Example 23 | Example 24 | |
Initial viscosity (ball) | 19 | 17 | 15 | 17 | 15 |
Viscosity (time/min) | 89 | 102 | 145 | 132 | 121 |
180 DEG peeling off [ N/25mm ]] | 12.3 | 12.6 | 14.4 | 13.2 | 13.5 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive in embodiments 25 to 29, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is ethyl acrylate, the hard monomer is styrene, and the crosslinking agent is glycidyl methacrylate, and the specific amount is shown in table 11.
TABLE 11
Raw materials (mol) | Example 25 | Example 26 | Example 27 | Example 28 | Example 29 |
Acrylic acid ethyl ester | 6.5 | 6 | 5.5 | 5 | 4.5 |
Acrylic acid pentafluorobenzyl ester | 2 | 2 | 2 | 2 | 2 |
Styrene (meth) acrylic acid ester | 1 | 1 | 1 | 1 | 1 |
Glycidyl methacrylate | 0.5 | 1 | 1.5 | 2 | 2.5 |
Azobisisobutyronitrile | 0.025 | 0.025 | 0.025 | 0.025 | 0.025 |
Ethyl acetate | 40 | 40 | 40 | 40 | 40 |
The same test methods as those used in examples 1 to 5 were used to test the performances of examples 25 to 29, and the related performances are shown in Table 12.
TABLE 12
Examples25 | Example 26 | Example 27 | Example 28 | Example 29 | |
Initial viscosity (ball) | 14 | 13 | 10 | 7 | 5 |
Viscosity (time/min) | 128 | 160 | 350 | 389 | 456 |
180 DEG peeling off [ N/25mm ]] | 13.3 | 13.8 | 14.3 | 14.3 | 15.4 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive in embodiments 30 to 34, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is ethyl acrylate, and no hard monomer and crosslinking agent are added, and the specific amount is shown in table 13.
Watch 13
The same test methods as those used in examples 1 to 5 were used to test the performances of examples 30 to 34, and the related performances are shown in Table 14.
TABLE 14
Example 30 | Example 31 | Example 32 | Example 33 | Example 34 | |
Initial viscosity (ball) | 20 | 22 | 19 | 15 | 13 |
Viscosity (time/min) | 60 | 123 | 143 | 178 | 188 |
180 DEG peeling off [ N/25mm ]] | 10.3 | 13.6 | 14.4 | 13.1 | 113.5 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive of embodiments 35 to 39, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is ethyl acrylate, no hard monomer is added, and the crosslinking agent is glycidyl methacrylate, and the specific amount is shown in table 15.
Watch 15
Raw materials (mol) | Example 35 | Example 36 | Example 37 | Example 38 | Example 39 |
Acrylic acid ethyl ester | 7 | 6 | 5 | 4 | 3 |
Glycidyl methacrylate | 1 | 2 | 3 | 4 | 5 |
Acrylic acid pentafluorobenzyl ester | 2 | 2 | 2 | 2 | 2 |
Azobisisobutyronitrile | 0.005 | 0.005 | 0.005 | 0.005 | 0.005 |
Ethyl acetate | 30 | 30 | 30 | 30 | 30 |
The same test methods as those used in examples 1 to 5 were used to test the performances of examples 35 to 39, and the related performances are shown in Table 16.
TABLE 16
Example 35 | Example 36 | Example 37 | Example 38 | Example 39 | |
Initial viscosity (ball) | 15 | 12 | 8 | 6 | 2 |
Viscosity (time/min) | 189 | 351 | 523 | 698 | 723 |
180 DEG peeling off [ N/25mm ]] | 13.3 | 14.1 | 15.2 | 15.5 | 16.7 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive in embodiments 40 to 44, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is isooctyl acrylate, the hard monomer is methyl methacrylate, and no crosslinking agent is added, and the specific amount is shown in table 17.
TABLE 17
Raw materials (mol) | Example 40 | EXAMPLE 41 | Example 42 | Example 43 | Example 44 |
Acrylic acid isooctyl ester | 3.5 | 3 | 2.5 | 2 | 1.5 |
Acrylic acid pentafluorobenzyl ester | 1 | 1 | 1 | 1 | 1 |
Methacrylic acid methyl ester | 0.5 | 1 | 1.5 | 2 | 2.5 |
Azobisisobutyronitrile | 0.001 | 0.001 | 0.001 | 0.001 | 0.001 |
Ethyl acetate | 15 | 15 | 15 | 15 | 15 |
The same test methods as those used in examples 1 to 5 were used to test the performances of examples 40 to 44, and the related performances are shown in Table 18.
Watch 18
Example 40 | EXAMPLE 41 | Example 42 | Example 43 | Example 44 | |
Initial viscosity (ball) | 17 | 15 | 14 | 11 | 10 |
Viscosity (time/min) | 55 | 68 | 90 | 132 | 143 |
180 DEG peeling off [ N/25mm ]] | 10.3 | 11.6 | 11.8 | 12.3 | 13.1 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive of embodiments 45 to 49, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is isooctyl acrylate, the hard monomer is styrene, and the crosslinking agent is glycidyl methacrylate, and the specific amounts are shown in table 19.
Watch 19
Raw materials (mol) | Example 45 | Example 46 | Example 47 | Example 48 | Example 49 |
Acrylic acid isooctyl ester | 3 | 2.5 | 2 | 1.5 | 1 |
Acrylic acid pentafluorobenzyl ester | 1 | 1 | 1 | 1 | 1 |
Glycidyl methacrylate | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
Styrene (meth) acrylic acid ester | 0.5 | 1 | 1.5 | 2 | 2.5 |
Azobisisobutyronitrile | 0.001 | 0.001 | 0.001 | 0.001 | 0.001 |
Ethyl acetate | 15 | 15 | 15 | 15 | 15 |
The same detection methods as those used in examples 1 to 5 were used to detect the properties of examples 45 to 49, and the properties are shown in Table 20.
Watch 20
Example 45 | Example 46 | Example 47 | Example 48 | Example 49 | |
Initial viscosity (ball) | 18 | 16 | 15 | 14 | 13 |
Viscosity (time/min) | 67 | 123 | 163 | 172 | 256 |
180 DEG peeling off [ N/25mm ]] | 10.5 | 11.6 | 12.1 | 13.7 | 13.9 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive in embodiments 50 to 54, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is isooctyl acrylate, and no hard monomer and crosslinking agent are added, and the specific amount is shown in table 21.
TABLE 21
Raw materials (mol) | Example 50 | Example 51 | Example 52 | Example 53 | Example 54 |
Acrylic acid isooctyl ester | 9 | 4 | 2.5 | 1.5 | 1 |
Acrylic acid pentafluorobenzyl ester | 1 | 1 | 1 | 1 | 1 |
Azobisisobutyronitrile | 0.05 | 0.025 | 0.0165 | 0.0125 | 0.01 |
Ethyl acetate | 40 | 20 | 13.2 | 10 | 8 |
The same test methods as those used in examples 1 to 5 were used to test the performances of examples 50 to 54, and the related performances are shown in Table 22.
TABLE 22
Example 50 | Example 51 | Example 52 | Example 53 | Example 54 | |
Initial viscosity (ball) | 22 | 20 | 21 | 21 | 17 |
Viscosity (time/min) | 67 | 115 | 143 | 172 | 188 |
180 DEG peeling off [ N/25mm ]] | 10.4 | 12.1 | 11.4 | 12.7 | 13.3 |
In the component a of the adhesive for the special fluorine-containing pressure-sensitive adhesive of embodiments 55 to 58, the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, the soft monomer is isooctyl acrylate, no hard monomer is added, and the crosslinking agent is glycidyl methacrylate, and the specific amount is shown in table 23.
TABLE 23
The same test methods as those used in examples 1 to 5 were used to test the performances of examples 55 to 58, and the related performances are shown in Table 24.
Watch 24
Example 55 | Example 56 | Example 57 | Example 58 | |
Initial viscosity (ball) | 18 | 15 | 6 | 3 |
Viscosity (time/min) | 62 | 73 | 88 | 140 |
180 DEG peeling off [ N/25mm ]] | 11.9 | 14.5 | 13.2 | 15 |
Meanwhile, the pressure-sensitive adhesive in the prior art is adopted as comparative examples 1-4, and the specific raw materials are shown in Table 25.
TABLE 25
Raw materials (mol) | Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 |
Acrylic acid butyl ester | 10 | 5 | 3.5 | 2.5 |
Methacrylic acid methyl ester | 5 | 2 | 1.5 | 1 |
Acrylic acid | 4 | 2 | 0.67 | 0.5 |
Acrylic acid dodecafluoroheptyl ester | 1 | 1 | 1 | 1 |
Dibenzoyl peroxide | 0.03 | 0.015 | 0.009 | 0.0075 |
Ethyl acetate | 60 | 30 | 18.2 | 15 |
Performance of comparative examples 1 to 4 was examined by the same examination method as in examples 1 to 5, and the correlation properties are shown in Table 26.
Watch 26
Comparative example 1 | Comparative example 2 | Comparative example 3 | Comparative example 4 | |
Initial viscosity (ball) | 6 | 6 | 7 | 7 |
Viscosity (time/min) | 55 | 75 | 80 | 95 |
180 DEG peeling off [ N/25mm ]] | 6 | 8 | 8 | 11.5 |
Comparing the performance tables of the comparative example and the examples, it can be seen that the initial adhesion, the permanent adhesion and the 180 DEG peel strength of the pressure-sensitive adhesive of the prior art are all weaker than those of the examples of the invention, which also shows that the special fluorine-containing pressure-sensitive adhesive of the invention has good re-stripping performance, higher peel strength, larger permanent adhesion and initial adhesion, and has no solvent discharge during the use and excellent adhesive performance.
Preparation of pentafluorobenzene-containing functional monomer
The invention discloses a pentafluorobenzene-containing functional monomer which is pentafluorobenzyl acrylate, and a preparation method thereof, wherein the preparation method comprises the following steps:
adding a fluorine-containing benzene structure compound and acrylic acid or acryloyl chloride into a reactor, heating for reaction, and extracting, cleaning and separating to obtain the monomer containing the pentafluorobenzene function.
Example 59:
calculating the components according to the molar mass ratio: putting a certain amount of acetone into a single-neck flask, adding 5-8mol of potassium carbonate suspended in the acetone, 1.5-4mol of acrylic acid, 1-2mol of benzyl pentafluorobromide and 0.1-0.3 mmol of 2, 6-di-tert-butyl-p-cresol. Condensing and refluxing for 3 hours at 65 ℃, completing the reaction, filtering the mixture, dissolving residues in diethyl ether, extracting with water, eluting a water phase with sodium bicarbonate and water, removing water from an organic phase with anhydrous sodium sulfate, distilling under reduced pressure to remove the solvent, and finally separating by utilizing column chromatography to obtain the product of pentafluorobenzyl acrylate.
The reaction formula is as follows:
example 60:
calculating the components according to the molar mass ratio: taking a certain amount of dichloromethane into a single-neck flask, adding 2-5mol of triethylamine, 2-4mol of acryloyl chloride and 1-3mol of pentafluorobenzyl alcohol, and reacting at room temperature for 2-3 hours to finish the reaction. Extracting, removing water from the organic phase by using anhydrous sodium sulfate, removing the solvent by reduced pressure distillation, and finally separating by utilizing a column chromatography to obtain the product of the pentafluorobenzyl acrylate.
The reaction formula is as follows:
preparation method of special fluorine-containing pressure-sensitive adhesive
The method for preparing the special fluorine-containing pressure-sensitive adhesive comprises the following steps:
(1) under the protection of argon, sequentially adding raw materials into a reactor for carrying out a sexual heating reaction, and then washing and drying to obtain a pure polymer;
(2) and (2) coating the polymer obtained in the step (1) on a fluorine-containing polymer material to obtain the special fluorine-containing pressure-sensitive adhesive. Wherein the fluoropolymer material in step (2) is a fluoropolymer membrane.
In specific implementation, argon is introduced into the reactor for 30min, raw materials are prepared according to the component proportion table of the embodiment 1-58, the solvent is divided into two parts with the same amount, wherein one part of the solvent, the soft monomer, the pentafluorobenzene ring functional monomer and the hard monomer are added into the reactor, and the mixture is heated to 75 ℃ for condensation reflux; and mixing the other part of solvent and an initiator to form a mixed solution, dividing the mixed solution into two parts with the same quantity, slowly dropwise adding one part of the mixed solution into the reactor, reacting for 4 hours after dropwise adding, continuously and slowly dropwise adding the rest of the mixed solution, reacting for 4 hours after dropwise adding, heating to 80 ℃, reacting for 3 hours, and ultrasonically washing for 3 times by using methanol after the reaction is finished. Drying for 10 hours at 65 ℃ in a vacuum drying environment to obtain pure fluorine-containing polymer. Coating the obtained polymer on a film of the fluorine-containing polymer material to obtain the special fluorine-containing pressure-sensitive adhesive. The coating may be a flat coating method, a knife coating method, a spin coating method, or the like, and the thickness of the fluoropolymer material film is 20 μm.
The performances of the special fluorine-containing pressure-sensitive adhesives of the embodiments 1-58 are tested, the initial adhesion of the embodiments is tested by using a GB-4852-1984 pressure-sensitive adhesive tape initial adhesion test method (rolling ball method), the permanent adhesion of the embodiments is tested by using a GB/T-4851-1998 adhesive tape permanent adhesion test method, and the peel strength of the embodiments is tested by using a GB/T-4851-1998 adhesive tape peel strength test method.
Finally, it should be noted that the above embodiments are only for illustrating the technical solutions of the present invention and not for limiting the technical solutions, and those skilled in the art should understand that those further modifications or equivalent substitutions to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions should be covered in the claims of the present invention.
Claims (10)
1. The special fluorine-containing pressure-sensitive adhesive is characterized by comprising an adhesive and a base material, wherein the adhesive is coated on one side surface of the base material; the adhesive comprises a component A and a component B;
the component A comprises the following components in percentage by mol: 5-50% of a pentafluorobenzene-containing functional monomer; the initiator is 0.1% -0.5%; the soft monomer accounts for 50% -95%; the hard monomer is 0% -50%; 0% -50% of a cross-linking agent;
the component B is a solvent, and the mole number of the component B is 3-8 times of the total mole number of the component A.
2. The special fluorine-containing pressure-sensitive adhesive as claimed in claim 1, wherein the pentafluorobenzene-containing functional monomer is pentafluorobenzyl acrylate, and the soft monomer comprises butyl acrylate, ethyl acrylate and isooctyl acrylate.
3. The special fluorine-containing pressure-sensitive adhesive as claimed in claim 1, wherein the hard monomer comprises methyl methacrylate and styrene.
4. The special fluorine-containing pressure-sensitive adhesive as claimed in claim 1, wherein the crosslinking agent is glycidyl methacrylate crosslinking agent.
5. The specialty fluorine-containing pressure sensitive adhesive of claim 1, wherein said initiator is azobisisobutyronitrile.
6. The specialty fluorine-containing pressure sensitive adhesive of claim 1, wherein said solvent is ethyl acetate.
7. A method for preparing a pentafluorobenzene-containing functional monomer according to claim 1, wherein the method comprises the steps of:
adding a fluorine-containing benzene structure compound and acrylic acid or acryloyl chloride into a reactor, heating for reaction, and extracting, cleaning and separating to obtain the monomer containing the pentafluorobenzene function.
8. The preparation method of the pentafluorobenzene-containing functional monomer according to claim 7, wherein the molar mass ratio of the fluorobenzene structure-containing compound to acrylic acid or acryloyl chloride is (1-3): (1-4) the reaction time is 2-3 h.
9. The preparation method of the special fluorine-containing pressure-sensitive adhesive is characterized by comprising the following steps:
(1) under the protection of argon, adding a solvent and other raw materials into a reactor according to the formula of the right 1-6, finally adding an initiator for heating reaction, and washing and drying to obtain a pure polymer;
(2) and (2) coating the polymer obtained in the step (1) on a fluorine-containing polymer material to obtain the special fluorine-containing pressure-sensitive adhesive.
10. The method for preparing special fluorine-containing pressure-sensitive adhesive according to claim 9, wherein the fluorine-containing polymer material in the step (2) is a fluorine-containing polymer film.
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